Boron tribromide → HCID 22921546, compound

HRID 2258626Notes

Reaction equation

HRID 2258626 reaction equation
B(Br)(Br)Br.[CH3:5][N:6]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][C:10](=[O:11])[N:9]([C:18]2[C:19]([F:36])=[C:20](C(COC)C)[C:21]3[NH:25][C:24]([C:26]([F:29])([F:28])[F:27])=[N:23][C:22]=3[CH:30]=2)[C:7]1=[O:8]>C(Cl)Cl>[F:29][C:26]([F:27])([F:28])[C:24]1[N:23]([CH:12]([CH3:13])[CH2:10][OH:11])[C:22]2[CH:30]=[C:18]([N:9]3[C:10](=[O:11])[CH:12]=[C:13]([C:14]([F:17])([F:15])[F:16])[N:6]([CH3:5])[C:7]3=[O:8])[C:19]([F:36])=[CH:20][C:21]=2[N:25]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178494895HCID 178494895, compound

Product 1

HCID 22921546HCID 22921546, compoundYield 189.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

One hundred mL of methylene chloride was stirred and cooled to about -40° C. To this was added dropwise 11.0 mL (0.011 mole) of boron tribromide (1.0M in methylene chloride). Upon completion of the addition, the reaction mixture was again cooled to -40° C., and a solution of 4.5 grams (0.010 mole) of 1-methyl-3-(1-methoxymethylethyl-2-trifluoromethyl-5-fluorobenzimidazol-6-yl)-6-trifluoromethyluracil (Compound 8--prepared in a manner analogous to that of Example 3) in about 20 mL of methylene chloride was added dropwise. Upon completion of the addition, the reaction mixture was stirred for an additional one hour at -40° C. After this time the reaction mixture was allowed to warm to ambient temperature, where it stirred for about 18 hours. The reaction mixture was then poured into a flask, and ice was added. The mixture was stirred until the ice melted, and then extracted with ethyl acetate. The combined extracts were washed with an aqueous solution saturated with sodium chloride and dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure, yielding 4.3 grams of 2-[2-trifluoromethyl-5-fluoro-6-(1-methyl-6-trifluoromethyluracil-3-yl)benzimidazol-1-yl]propan-1-ol. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was again cooled to -40° C.
  3. additionwas added dropwise
  4. additionUpon completion of the addition
  5. temperatureto warm to ambient temperature
  6. stirringwhere it stirred for about 18 hours
  7. additionThe reaction mixture was then poured into a flask
  8. additionice was added
  9. extractionextracted with ethyl acetate
  10. washThe combined extracts were washed with an aqueous solution saturated with sodium chloride
  11. dry with materialdried with magnesium sulfate
  12. filtrationThe mixture was filtered
  13. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-712cabfb126d4600b69d922b30ea306c
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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